10 Best Skyzoo Songs to Help You Appreciate His Lyrical Genius

The era of rap blogs being a fundamental foundation for music discovery was the best of times for young hip-hop enthusiasts. Blogs made it possible to find artists that radio didn't care about, the superb underground talent that cared more about upholding the essence of wizardry in wordplay and lyrical miracles instead of following whatever Top 40 jingle was conquering the world. There was always hope that one of these deserving emcees would be embraced and beloved for what they were contributing to the culture. Sadly, time and time again, the best and brightest continued to operate under the dim spotlight that barely breaks through the thick cracks of the underground.

The blogs introduced me to Brooklyn-born and Brooklyn-raised emcee Gregory Taylor, better known as Skyzoo. Since 2009―when he released his debut album, Salvation―I've been waiting for the world to wake up. I think of Skyzoo whenever I hear complaints about New York hip-hop not living up to the standards of its forefathers. I think of Skyzoo when I read tweets about the lack of lyricists who weave meaningful bars with vivid storytelling, still capable of impressive punchlines and metaphors. I think of Skyzoo each time the words “real hip-hop” are said in my presence. I'm always left wondering why the complainers aren’t uplifting him. He is the full-package offspring of New York’s lineage of lyricists that have consistently tattooed great production with bars. A rapper’s rapper.

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Like many of his die-hard fans, I was drawn to the way he could produce stories of corner boys without leaning on Southern trap. The way he could rip a 9th Wonder soul sample with the same tenacity of a !llmind drum break. Skyzoo is one of the few rappers who can record an Ode to Reasonable Doubt doing justice to Jay’s debut classic and make a concept album stepping into the shoes of Theo Huxtable and J.J. Evans.

I’m not the biggest fan of his hooks―which is what you need to survive in this modern era―but with an excellent ear for beats that sit comfortably between vintage and modern, and the ability to continue rhyming at a top-tier level almost 10 years after his critically acclaimed debut, I find it impossible not to think of Skyzoo as one of hip-hop’s most skilled and underrated artists.

Complaining about the lack of attention an artist receives does nothing but the raise blood pressure of the woke and irritate the sleepy. So instead of telling people how dope Skyzoo is, let's let the music speak for itself. Hopefully, awareness will be raised and new listeners will feel compelled to give his new EP, Peddler Themes, a deserving listen.

Together with fellow DJBooth scribe and Skyzoo enthusiast Dylan (aka CineMasai), here are 10 of Skyzoo's best songs from his massive discography, listed in chronological order.

"Stop Fooling Yourself" (Cloud 9: The 3 Day High w/ 9th Wonder, 2006)

Sky can be flashy when he feels like it, but his stories cut even deeper when they’re blunt. “I solemnly swear, what I perform in the booth / All of it is truth,” he breathes into the mic on the opening of the tragic “Stop Fooling Yourself.” Here, Sky laments the life of a drug dealer who’s hell-bent on straightening up and heading to college only to find his friends and even God laughing in his face (“Wasn’t you the same motherfucker / That showed us how to cook up and cut the butter?”) over an expertly chopped refrain from 9th Wonder. I can hear Sky physically ripping his NC Central acceptance letter in half every time.

It’s a story powerful in its simplicity; is a man dooming himself to running the streets forever no longer fooling himself? I think of this question every time I revisit J. Cole’s “‘03 Adolescence,” another story of a kid who almost threw his life away just to impress his friends. I can’t help but hear a street-weary Sky on the couch telling Cole to chase that degree instead of moving weight for “a hundred bucks or two a week” and cursing his parents for not wearing rubbers. Cole took the advice that Sky ignored, but Sky’s perspective over 9th Wonder’s lush thump of a beat almost yanked tears out of my eyes. — CineMasai

"The Beautiful Decay" (The Salvation, 2009)

9th Wonder and 2DopeBoyz put Skyzoo on my radar. 9th’s early stamp and Shake’s enthusiastic posts about his music is what inspired me to press play. “The Beautiful Decay” is one of of the 10 songs that 9th had a hand in producing on Sky’s The Salvation. The soulful loop of The Sylvers “How Love Hurts” is like having an angel humming in your eardrums. 9th gave Sky a wall to graffiti over. The entire song feels like a tagger painting a picture of the world he lives within. Imagery is excellent, every line adds to the sketch. It’s a love letter to the past and present, to the beauty of home and the decay. You can’t have one without the other. Accepting where you come from for all it’s good and all the bad. — Yoh

"Inheritance" (The Great Debater, 2011)

"And anything that that entails / Catch the tail end of this / And you’ll be playing Kit to TaleSpin with this / ‘til they fear remembering / Pretend that it ain’t made you yet / Higher For Hire through Cape Suzette"

I lost my mind. He pulled out an extended metaphor in reference to a series I haven’t seen since I was like seven years old. Kit is the character, TaleSpin is the series name, Higher For Hire is the company he worked for, and Cape Suzette is the city the series was based in. The entire song will be appreciated by anyone who enjoys a rapper manipulating words like a master ventriloquist manipulates puppets. Sky gives you the thrill of hearing a rapper execute bars you never expected to hear and likely will never hear again. The way he’s able to weave references of TaleSpin, The Wire, or Juice into his lyrics shows a master class rapper and pop culture devotee. He makes dissecting lines and rewinding lyrics a necessary part of the listening experience. — Yoh

"Fulfillment” (Theo vs. J.J. (Dreams vs. Reality), 2012)

What do Nas and Mase have in common? Aside from being New York down to the blacktop, they both stand at either end of the middle ground Sky feels that he occupies. “Half ‘94 Nas, half ‘97 Betha,” he claims at the start of “Fulfillment.” Theo vs. J.J. is a balancing act between lavish Huxtable dreams and a Good Times harsher reality that “Fulfillment” nails, right down to the oscillating beat courtesy of Thelonious Martin. Sky is happy that he only has to call his lawyer to look over contracts but still watches as his block gets gentrified. The hustle to get the keys to that Brooklyn brownstone is never-ending, and “Fulfillment” is the first step on a 12-track album toward getting there. — CineMasai

"Steel’s Apartment” (A Dream Deferred, 2012)

As an emcee with a cinematic pen, it’s no surprise that Skyzoo finds tons of inspiration in film. With “Steel’s Apartment”—a deep cut from 2012’s A Dream Deferred—Sky found a parallel between his friends growing up and the crew in the Tupac flick Juice; the feeling of days spent staring down gun barrels, penning rhymes and drinking 40s in 40-degree weather (“Bigger dreams penciled in, Hennessey adrenaline / Throw down, stand up and die for it like Blizzard did”). Sky lays down the hopes, dreams and fears lurking outside the doors of home base apartments over Black Milk's billowing horns and sturdy drums.

The song is peppered with clever lyrical nods to Juice and Pac’s music, but the sense of atmosphere keeps the listener in this song’s orbit. I can smell the lobster fried rice Sky and his friends pick up on the block every time I revisit “Steel’s Apartment.” — CineMasai

"Floor Seats With Young” (Band Practice, 2013)

2013 was the year Sky decided to bring in a seven-piece jazz band for a performance of catalog classics at MIST Harlem. To build anticipation, the Brooklyn lyricist started the Band Practice series, the release of four new songs performed atop jazz compositions. Being a sucker for royal horns and rap flows smoother than T.I. on roller skates, a natural favorite is “Floor Seats With Young.” My favorite line, “Lil road kill, ID 'em by they jewelry,” is just one of the many memorable moments littered throughout the song. Not a single bar is wasted, the kind of rhyming that Genius was made for.

To know Skyzoo is to know his admiration for JAY-Z, and one of my favorite lines captures being a fan and being in competition with an idol:

"Just a dude from Brooklyn who had intentions / Of hoping that Jay is watching and saying 'Yeah, he gets it' / But hoping that Jay is watching is double-edged and twisted / Like, 'Yeah, I'm still a fan but now I'm within the business'"

Skyzoo is one rapper who will never have to record a song about letting JAY-Z down. — Yoh

“I blew money on bottles while standing next to the rappers who had deals with budgets on stand still, it really happened” is such a Hov line. Being a student of those that came before him, Sky was perfect to recreate Reasonable Doubt the way Elzhi did Illmatic. Philadelphia composer AntMan Wonder reworked the classic album with an assortment of live instrumentation that brought familiar beats a brand new sheen and Sky’s rhymes weave his perspective with Easter egg moments from the source material. It’s an admirable hat tip to the project that introduced JAY-Z back in ‘96. As a whole, the entire album is worth revisiting, but “The Usual Politics” is executed with sharpshooter precision. From the strings to Sky’s perspective, it gives you nostalgia for Hov while enjoying the new variation. Classics can’t be replaced or replicated, but honorable renditions will always be appreciated. Sky did Jay justice. — Yoh

"All In Together” ft. Random Axe (Barrel Brothers w/ Torae, 2014)

Barrel Brothers are a duo that feeds into each other’s strengths. Skyzoo's nonchalance on the mic is the setup that dovetails perfectly with Coney Island wordsmith Torae’s hard-nosed bruising. The group’s self-titled 2014 album made ample room for the pair to bounce off of breakbeats and each other, but “All In Together” is their most potent offering. Torae chews the first verse to shreds, but Sky falls in the pocket on the back half with jaw-dropping wordplay. The force behind “Shuttlesworth and Buttersworth on a shooting spree / Sharpshooter, park shooters, part the Cs” is simultaneously fluid and as hard as a manhole cover to the face. Managing to out-nasty veteran mean muggers Guilty Simpson and Sean Price is no small feat, either. — CineMasai

"On The Stretch & Bob Show" (The Easy Truth w/ Apollo Brown, 2016)

Skyzoo and Detroit producer Apollo Brown are kindred hip-hop spirits. Brown specializes in the kind of dusty soul loops and ear-shattering low end vibes that Sky’s rhymes were born to share the stage with. Their mutually beneficial skills finally met halfway on last year’s joint album, The Easy Truth, but nowhere is this more prevalent than on the album’s centerpiece, “On The Stretch & Bob Show.” You don’t just insert yourself into an old episode of Stretch Armstrong and Bobbito Garcia’s legendary radio show (a Nas episode, no less!) unless you’ve got the skills to back it up. Over radio static and a disarmingly simple breakbeat, Sky lets one-liners fall like pennies: “I’m part Ives Saint Laurent and part panther,” “Sympathy aside, y’all will go in the trunk / My bio is Riley Freeman meets Thelonious Monk," “And whether we talkin’ pens or we get to talkin’ limbs / We still talkin’ how I’m walking XXL.”

This isn’t just two connoisseurs of '90s rap creating their own fan fiction. This is Skyzoo tipping his hat to the legends while re-staking his claim as a first-rate storyteller, weaving together internal rhymes and references to Child’s Play, Supreme, the Golden State Warriors and the Quran and barely breaking a sweat while doing it; or in his own words: “This is more or less battery acid on the Notes app.” He might need an actual guest spot on the new Stretch & Bob podcast for this one. — CineMasai

"Bamboo” (Peddler Themes, 2017)

When I was a two-year-old rugrat, HBO produced a movie called Strapped. The premise revolves around an ex-con turned arms dealer who is selling guns as a police informant. With a cast full of rappers—Yo-Yo, Busta Rhymes, Chi Ali, Kool Moe Dee, Monie Love, Fredro Starr―you would think BET would air it regularly like Baby Boy or Love & Basketball. Skyzoo draws inspiration from the hip-hop flick with “Bamboo,” a single from his new Peddler Themes EP. The thin, fluttering sounds of congas and gorgeous, lush horns create an instantly cinematic atmosphere as if you’re in a Spike Lee film from the ‘90s. Marc Nfinit's production is a jazzy throwback canvas for Sky to take us into the black market of arms dealing. It’s immaculate from beginning to end, an excellent way to pay homage to the past and flex the storytelling muscle. Take note of clever references to Ruthless Records, Amel Larrieux and Fab 5 apparel. Also, the imagery of a gun seller receiving reviews on Yelp is hilariously modern. A great introduction to Skyzoo for anyone late to the party. — Yoh